In spite of the fact that the Present-Day English “adverbial signature” – the suffix ‑ly – is peculiar to English among the Germanic languages and that its emergence seems to conflict with general tendencies of language change in English – the loss of inflectional endings and the fact that English is otherwise happy to allow zero-derivation – neither the early history of ‑ly in Old and Middle English nor the exact date and reasons for its remarkable spread have been fully understood. Recently, the subjective semantics of adverbs in ‑ly have received considerable attention, in both synchronic and diachronic studies. This claim for a particular subjective (abstract or figurative) meaning of adverbs in ‑ly, however, rests almost exclusively one study, Donner’s lexicographical examination of MED material (1991). This chapter inspects the potential of comprehensive textual studies for the suggested subjective semantics in the early use of ‑ly, focussing on two late Old English translations of the Theodulfi Capitula and the early Middle English poem The Owl and the Nightingale, one of the earliest idiomatic and colloquial English texts.